Total Synthesis of (+)-laurencin: An Asymmetric Alkylation - Ring-closing Metathesis Approach to Medium Ring Ethers

Michael T. Crimmins, Kyle A. Emmitte

Research output: Contribution to journalArticle

122 Scopus citations

Abstract

(Matrix resented) The enantioselective total synthesis of (+)-laurencin 1 is achieved in 18 steps from (S)-(+)-4-benzyl-3-benzyloxyacetyl-2-oxazolidinone. The key steps in this synthesis are an asymmetric glycolate alkylation leading to acyl oxazolidinone 2 and a subsequent ring-closing olefin metathesis to construct the oxocene core of 1. The approach to medium ring ethers utilized in this synthesis provides a general and efficient route to the cyclic core of other marine natural products.

Original languageEnglish
Pages (from-to)2029-2032
Number of pages4
JournalOrganic Letters
Volume1
Issue number12
DOIs
StatePublished - 16 Dec 1999

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